That's a good point. They're planning to retire in about 8-10 years, and I think their retirement income will put them around the 22-24% bracket based on their pension and expected 401k/IRA withdrawals. So it sounds like pre-tax contributions still make sense now, especially in 2023 if they're in the 24% bracket. But doesn't that still leave the question of whether to do the SEP for 2023 vs. prioritizing backdoor Roth going forward? The SEP would block backdoor Roth unless we convert it (paying taxes again).

If their retirement tax bracket is expected to be 22-24%, then yes, pre-tax contributions make sense now, especially while they're still in the 24% bracket. For your specific question about 2023 SEP vs. future backdoor Roth, I'd recommend a hybrid approach. Have your dad make a SEP contribution for 2023, but perhaps not the full $12,889. He could contribute just enough to keep him from spilling into a higher bracket. This gives some tax savings now while limiting the amount that would affect future backdoor Roth conversions. Then for 2024 and beyond, focus on maxing out his employer 401k (including any after-tax contributions for mega backdoor Roth) before considering backdoor Roth IRA strategies. The 401k contributions would give him the pre-tax benefit without the pro-rata complications of the SEP.

This is a really good point about being near the bracket edge. Moving from 24% to 32% is an 8% jump which is huge. If a $12,889 SEP contribution could keep them in the lower bracket for 2024, that would save significantly more than just the direct tax benefit on the contribution itself.

That's actually a fantastic point I hadn't considered! They're definitely near the edge of the bracket - I think my mom estimated they'll be about $15-20k over the 24% threshold for 2024 without any additional deductions. So a $12,889 SEP contribution for 2023 wouldn't directly affect 2024 taxes, but it would free up cash they could use for other deductions or opportunities in 2024. I'll definitely bring this up with them - maybe they could increase 401k contributions enough in 2024 to stay in the 24% bracket if they preserve more cash now with the SEP contribution for 2023. Thanks for this perspective!

What exactly is the pro-rata rule? I've been doing backdoor Roth for 2 years but have an old traditional IRA with about $30k in it. Should I be worried?

Yes, you should definitely be concerned. The pro-rata rule means you can't just convert your non-deductible contributions tax-free if you have other pre-tax IRA money. The IRS looks at all your IRA accounts (traditional, SEP, SIMPLE) as one big pot when you do a conversion. The taxable portion is calculated based on the ratio of pre-tax money to the total IRA balance. So if 80% of your total IRA money is pre-tax, then 80% of any conversion will be taxable regardless of which specific dollars you're converting.

TurboTax actually handles this pretty well but it's not obvious. You need to go to the IRA contributions section and make sure you select "nondeductible contributions." It'll then walk you through Form 8606. Just make sure you indicate which tax year the contribution was for. For the conversion, that goes in a separate section under "IRA distributions.

Good point about state taxes! I'm in Illinois and haven't even thought about that side of things. Would I use the same 1040-ES form to calculate what I might owe the state, or is there a separate process for that?

For state taxes, you'll need to use your state's specific forms, not the federal 1040-ES. Each state has its own estimated tax forms and procedures. For Illinois, you'll want to look up form IL-1040-ES, which is their estimated tax payment form. States also have different thresholds and requirements for when you need to make estimated payments. Some states follow the federal safe harbor rules, while others have their own unique requirements. I'd recommend checking the Illinois Department of Revenue website or giving them a call to confirm their specific rules about estimated taxes for self-employment income.

Is the self-employment tax deduction an itemized deduction or can you take it even if you use the standard deduction?

This is so helpful! So basically if I have a single-member LLC, the IRS treats me exactly the same as if I just had a sole proprietorship? What's the advantage of multi-member then? My wife and I are thinking of starting a business together.

That's right - for tax purposes, a single-member LLC is treated exactly like a sole proprietorship. You file Schedule C with your personal return, and the LLC is completely "invisible" to the IRS. For you and your wife, it depends on your state. In community property states, a husband and wife can elect to treat their LLC as a disregarded entity (essentially a sole proprietorship) instead of a partnership, which simplifies filing. In non-community property states, a husband-wife LLC typically files as a partnership, which means a separate tax return (Form 1065) and Schedule K-1s. The partnership route involves more paperwork but can sometimes offer more flexibility in how income and expenses are allocated between owners.

You actually don't need an LLC to deduct legitimate business expenses. You can deduct the business portion of your computer, internet, home office space, and business travel on Schedule C as a sole proprietor. The LLC won't change what you can deduct - you just need to make sure they're ordinary and necessary expenses for your business.

How's the reporting feature? I need to be able to generate reports for specific time periods or clients.

The reporting is actually one of its strongest features. You can generate reports by client, project, time period, expense category - pretty much any way you want to slice the data. I run quarterly P&L reports for my own tax planning, but also generate client-specific expense reports when I need to justify certain pass-through costs. They've also added a dashboard feature that gives you a real-time view of outstanding invoices, expenses by category, and profitability by client. I check it weekly to make sure I'm staying on track with my financial goals.

I used Everlance for about 6 months. It's decent for mileage tracking but pretty basic for everything else. The automatic trip detection was hit or miss for me - sometimes it would record random trips when I was just sitting at my desk! The receipt scanning is okay but not great for complex receipts. If your needs are simple and mainly mileage-focused it might work, but I switched to something more comprehensive.

Thanks for the insight! Sounds like it might not be robust enough for what I need. I've got a lot of different expense types beyond just mileage.